Business Transactions and Contracts
by LynnLockhart
Summary: Crowley needs help getting rid of an upcoming threat to him and his throne in Hell, but this time, the Winchesters (a.k.a denim wrapped nightmares) aren't going to be enough. Luckily Crowley remembers an old deal that could prove to be his salvation. Will she agree to this newfound way out of her deal and regain her soul or will Crowley murder the insufferable woman before hand?
1. Chapter 1

**Crowley needs help getting rid of an upcoming threat to him and his throne in Hell, but this time, the Winchesters (a.k.a denim wrapped nightmares) aren't going to be enough. Luckily Crowley remembers an old deal that could prove to be his salvation. Will she agree to this newfound way out of her deal and regain her soul or will Crowley murder the insufferable woman before she had a chance to help them by doing what she does best? Killing. (Disclaimer I do NOT own Supernatural but if I did I would be trolling with Destiel feels w)**

Dean gasped and bent over, hands on his knees in the classic world renown 'I'm either going to vomit on my shoes or pass out, either way it's about to get messy' position. Once his head cleared her looked up to find Bobby and Sam in similar situations and noticed for the first time where they were. Standing up shakily Dean did a full three-sixty as he took in their surroundings. They were in the middle of a crossroads, gravel going straight on for as far as he could see, and the only other signs of life were the horses a little ways away grazing unknowingly with little to no care.

"Well now that wasn't so bad was it?" The three men turned to the British bastard that appeared right behind them.

"Cristo, do you always have to appear behind people?!" Crowley flinched, his eyes turning jet black before he ground his teeth and smiled tightly at Sam.

"If I were you boy," he stepped forward threateningly causing Dean to step forward at his brother's side and Bobby at his other, "I wouldn't say that to often around me. It makes me antsy." They stood like that for a few minutes, just having a stare down before Deans' impatience got the best of him and he scuffed his feet.

"Well what now?" Dean asked impatiently.

"Now," Crowley retorted sarcastically, "You get to stand there and look pretty while I call my darling Juliet." He brings his fingers up to his mouth ready to whistle.

"Hello there!" they jump and turn to look at the unexpected voice. A young woman with pale blue doe eyes, dark brown hair reaching just below her lower back wearing a too big jean jacket, worn blue joins, and steel toed boots stood there looking very smug, no doubt enjoying scaring them. She held up her hands submissively, "Don't worry, I'm not the demon. I'm here to have my soul collected. Sorry for causing you any heart malfunctions." She chuckled, obviously **not** sorry whatsoever. Crowley looked at her hard and she returned the gaze as recognition dawned on her face. "Ah! You're a bit early there bub. I've got twenty minutes and I'll not have you cheating me out of a single second!" she pointed her finger at him jokingly, smiling as he finally seemed to remember her. "Yeah, sorry I've grown a bit since we last met. Don't worry, I wouldn't recognize me either from ten years ago." She laughed and Sam turned to Crowley.

" **That** is the girl you mentioned?" he demanded. Crowley seemed a bit irritated with his tone but nodded his head, too flabbergasted to actually respond with a cutting retort.

"The **hell** you doing here kid?!" Bobby yelled, startling her. She narrowed her eyes confused.

"Beg 'pardon, sir?" She asked politely and Bobby widened his eyes at her.

"Did I stutter? You do realize that this bastard here," he jabbed his hands towards Crowley who watching the conversation with eager eyes, "is going to take your soul tonight?" She drew her eyebrows together more and shifted her weight into a more defensive position.

"Uh, well sir, I'm not sure how that's any of your business but… yes that's right." Bobby blinked at her and waved his hands to the side.

"You realize that the thing that's going to take your soul –a Hellhound- is gonna rip you apart to the point that they'll have to identify you by your dental records before actually killing you?" her eyes widened slightly at that and Dean and Sam shot him a look.

"Well by all means don't sugar coat it for her." Dean shouted at him.

"That was a bit harsh even for you Bobby." Bobby turned to them sarcasm dripping from his face.

"Well boo-hoo! Sorry that I hurt your feelings **princess**."

"Wow Hellhounds? Is that true?" The lady directed the question at Crowley and he nodded and shrugged his shoulders. "Huh…well shit." she muttered to herself, exhaling slowly and the three men sighed- maybe she did have common sense. "Well!" She shouted clapping her hands together and smiling to herself when they jumped, "guess that means I better hurry! No telling when those shits might turn up- no offense to you or your mutts. I was gonna have a little picnic while I waited but looks like it's gonna have to be fast food…" They watched her in silent awe as she took out a small cooler, a couple forks and small plates, and a pie (Dean automatically identified it as blueberry). As she finished emptying the bag she looked up at them expectantly and patted the ground, "Well come on, I don't bite! I made a deal with the Devil, I didn't become one. Besides," she pulled the lid off the cooler with apparent ease and brought out a cold glass from within the ice singing, "I have free be-er." At first no one moved but then Bobby shrugged his shoulders and came to sit besides her making Dean and Sam follow but hesitantly. She smiled up at them as she handed them each their beer and reached into her pocket after they were settled. She flipped open a pocketknife causing Dean and Sam to straighten before she started cutting out five pieces of pie and dishing them up onto the small plates. Bobby cleared his throat and held out a hand.

"Well, not that I don't like eating with strangers but I'm Bobby." The girl smiled and took his calloused hand eagerly.

"They call me Ollie." Bobby nodded gruffly before leaning back and taking a swig of beer. Dean tried speaking up but had his mouth full of pie at the time.

"Nife ta me'tch-ew Owwie. Ma 'Ames-"

"This one, who doesn't have any manners," Bobby stared pointedly at Dean who grunted indignantly at the insult, "is Dean. The one **not** being an idjit is Sam, and I don't think I need to introduce Crowley." Crowley, who refused to sit down and dirty his suite, grinned tight-lipped at Bobby before switching to a charming smirk as he faced towards the lady.

"A pleasure to have done business with you, Darling." Ollie smiled widely and ducked her head at him before looking back and offering Bobby a piece of pie, oblivious to Crowley's disgruntled expression her politeness had caused.

Bobby took another sip of beer before twisting it into the dirt –couldn't have it spilling after all- and taking the little plate from her with a gruff 'thanks'. Once she was sure he approved of it she got out a bottle of Whiskey and deliberately threw her head back and downed what should have been at least seven shots. Dean finally managed to clear his mouth and whistled.

"Well now we know why you aren't freaking out." He smiled cheekily at her and she threw her head back laughing.

"Well I'm sorry to disappoint you but this," she wiggled the now half empty bottle, "has nothing to do with why I'm calm. Besides I ain't one of those cheap fruity drink loving sleaze balls that you're probably used to." She smirked into her whiskey as Dean ducked his head at Bobby and Sam's laughter, and even Crowley's chuckle. "But since we're on the topic," she let her smile fall away and stared at Crowley intensely, "Why did you come here? I can gather that they found out about my deal from you, but I don't understand why you'd be interested in me unless it was to collect my soul earlier then scheduled." A thought seemed to come to her and she looked up at him fearfully, "The deals not off is it?" Crowley chuckled good-naturedly and walked over until he was staring right down at her.

"No, no nothing of that sort. I'm actually here to make you a counter offer." She cocked her head to the side, much like Cas did when he was confused.

"Oh?" he nodded his head encouragingly. She cocked her head the other way before shaking it sadly, "Sorry but no thank you. I'm not interested." Once again Crowley stared at her in bewilderment as she seemed to focus all too much on the piece of pie she was now devouring.

"That's it?" she looked up startled at the demon's outburst and swallowed her pie to answer him, "Just 'No thank you I'm not interested'?" she pursed her lips thoughtfully before nodding and turning to him.

"Ye-p." she popped the 'p' and went back into the cooler to take out two more beers for Dean and Bobby. She put their empty glasses back in and pulled a bottle of Crown Royal from the cooler this time, consuming it like she had the whiskey. "However," she put down the bottle and scooted over patting the spot beside her, "I'd be willing to listen if you sat down and had some pie." The smile on her face was all too innocent, Crowley decided.

"And get my suite dirty? Not to mention how uncomfortable sitting in gravel is?" she shrugged and with one fluid motion took off her jean jacket and patted it. Crowley squinted at her like she had sprouted two heads.

"And that magic jacket of yours is going to solve what exactly my Dear?" much to the hunters amusement she actually rolled her eyes at him.

"Ugh! You should have told me you were coming before hand, I would have brought some cheese for your whine." Sam snorted on his beer and Dean out right laughed and patted Ollie on the knee.

"Damn, I like you! Too bad you made a deal with this douche-" _whack!_ The sound echoed through the clearing as both Sam and Dean's heads were knocked forward by Crowley. Dean held the back of his head while Sam just groaned. "Damn Crowley, you said **we** couldn't take a joke-" _whack!_ Dean actually had the good grace to keep his pie hole shut the second time as Bobby and Ollie watched amused

"Idjits." Bobby shook his head and polished off half the beer he had just been given. Ollie laughed and Bobby had to admit, the kid was something else. Bobby looked up at Crowley, "You know if she really can help us out the least you can do is sit on a damn jacket." The Demon in question raised his eyebrows at Bobby as if he had just offended his suites.

"I'll have you know, Singer, that this suite costs more then anything on all of you combined." Ollie scoffed at him and reached into her bag to pull out a bottle of scotch, displaying it like a game show host. He stared at it greedily for a moment and she then reached into the cooler and pulled out a crystal glass in which sat a few ice cubes. Crowley 'tsked' at her bribery and Bobby, Dean, and Sam watched in fascination as Ollie wiggled her eyebrows at him suggestively. After a few tense moments in which the hunters thought for sure she was going to be hurt Crowley let out a large sigh, "Oh alright you've got me, now scoot over." the effect was immediate and she smiled brightly at him, happy to comply watching as he settled down, "Hades, I told you this wouldn't be comfortable. I could count the number of stones poking into my- oh!" he was interrupted as Ollie thrust the bottle towards him and he looked at it in amazement, "is this a two hundred year old bottle of Craig?" he looked over at her as she just shrugged her shoulders modestly and dished up the last piece of pie and handed it to him. He reluctantly put down his newfound friend in favor of the pie and hummed his approval of the first bite, not taking his eyes off the bottle, "How in the world did you come by something like that?"

"I take it I got the right kind then?" He finally relinquished his staring contest with it to turn to her inquisitively. She took another swig of Crown Royal before answering, "ten years ago during our deal you had a glass in your hands and I asked you what you were drinking. You said 'the good stuff, Love. They don't make scotch like they used to'," She quoted, making Dean snicker at her terrible impression of Crowley, "I asked you what year and you said '18-something'. I couldn't remember what year –still can't actually- but I remember you claiming you were running low. I saw that beauty on a job and figured you'd need the pick me up next time we met." She smiled as she finished her story and started collecting the plastic plates and forks from everyone as they finished. She replaced Sam's finally empty beer and replaced it with the last one before putting everything back in her bag.

"Hey, Dean could you do me a favor?" without waiting for an answer she slid the bag towards him and he grabbed it reluctantly, "Throw that away for me on your way out? I'd hate to just leave trash hanging around." Dean nodded speechless and looked over at Sam who leaned forward a bit as he spoke.

"You work with old liquor?" Ollie nearly spat out her drink as she struggled not to choke on it.

"Oh god no!" she laughed, "With a job like that, I'd probably end up more of an alcoholic then I already am." Sam started to ask her what her job was but she spoke up before he could open his mouth. "I'm a contract killer." Booby actually did spit out his beer and Crowley choked on his drink at Bobby's reaction while Dean and Sam both looked at her astonished. She glared playfully at them, "Don't worry, not like in movies or anything. I do my research before hand and if the client comes back clean I kill the employer." Bobby raised his eyebrows at her, "Well I can't exactly walk into their office and say 'Hey you dick he or she was clean so I'm bugging out. Here's your money back and have a nice day'." She deadpanned taking a last drought of her drink while Bobby looked to Crowley accusingly.

"You didn't think that would be a good thing to tell us?" Crowley scoffed at him.

"Would you have come unarmed if I had told you?" Bobby nodded resignedly as he tried to drink his beer to find that it was empty. He sighed and passed it to Dean who put it back in the bag, still staring at Ollie who passed around her empty bottle as well.

"Now," turning to Crowley she smiled attentively, "I believe I promised to listen to your 'counter offer'." She made quotas in the air as she said the last part and Crowley had to admit- the girl was something else, sitting here with three strangers and a Demon- of course if she new he was the king of Hell maybe she wouldn't be so familiar with him.

"Yes well, my 'counter offer'," he wiggled his fingers in the air mockingly, "as you so eloquently put it, is a bit hard to explain so please leave all questions until the end of the lecture." She chuckled and shook her head. "I mean it." Crowley threatened. Ollie rolled her eyes and motioned for him to continue. _Impatient woman_ , Crowley mused. "We are in need of your assistance in the matter of taking down a certain corporation. Now this operation of sorts is a small piece of a bigger picture and in order to accomplish said bigger picture-"

" **P-fffffffff-t!** " Crowley looked like he was either going to scream or kill her.

"Did you just interrupt me with a-"

" **P-fffffffff-t!** " She raspberries again and the three hunters stiffened, readying themselves to have to stop Crowley from murdering the dumb broad. Who the hell interrupts the King of Hell with a raspberry?! "Look I get that you probably have a good monologue planned out but honestly that shit puts me off in the worst way possible. Now," she held up a hand as Crowley started talking, silencing him and making Bobby smile, "if the King of Hell- and yes I know who you are, I'm not a complete idiot- is asking a favor of **me** to kill someone then it's obviously not human. When I make a deal with a client- ha, ha." Crowley looked at her like she was crazy and she looked around smiling cheekily, "oh, come on, you don't see the irony in that?" Dean chuckled and nodded approvingly while Sam and Bobby just shook their heads- Crowley seemed to be in a state of shock of some kind so she waved away the other two hunters judgmental stares, "Whatever I'm hilarious- anyway so when I make the deal I have three criteria's that need to be met and satisfied before actually doing anything. First thing on the list is research; everything from routine to family history including happenings and deals as far back as you can get them. I need to know if they have any ties with mafias or anyone with power, I don't intend on having anyone –or thing apparently- coming home to bite me in the ass on my way out the back door. Second thing is recognition; I take what they do in the public and accumulate exactly what they do behind closed curtains and if they have any evil skeletons in the closet –when I say evil I mean this better be one mean mo-fo cause I don't kill for anything less then Ted Bundy. Stage three is the 'method of ending'; more times then not I end up being hired by the mafia or cartel and those bastards are sassy and like sending out messages. However that's not the case this go around so you're going to have to help get the necessary equipment to gank the S-O-B's" She looked around her at their faces and pouted. "What? I can't be professional **and** know how to enjoy the small things? That's pretty bigoted of you boys, I'm hurt- wounded even!" Crowley scoffed and put down his finished glass, _I'm already regretting this_ , he thought wearily.

"Yes, well that all makes sense. Now as for your payment," he snapped his fingers and a piece of parchment appeared, "You get your soul back." Ollie's expression changed instantly. Her eyes became dim as a memory of some kind danced across her vision and for a moment Crowley thought she was about to kill something- or more importantly him. She shook it off and looked over at him cautiously.

"If you return my soul, what happens to my previous deal?" Crowley smiled understanding her hesitation.

"Ah! Yes well it will still remain in effect. Nothing could break that deal unless you should double cross us." her expression softened and Crowley let out a breath he'd been holding unknowingly. _'Why am I so on edge? She's just a human- pull yourself together you imbecile.'_ She nodded her head and smiled brightly- unaware of the demons internal debate.

"No wonder you're the King of hell," she muttered before clearing her throat, "You've got yourself another deal." Crowley smiled and stood to his feet, holding out his hand to help her up. She looked a bit surprised at his offer –he was as well though he didn't show it. She smiled even wider, if that was possible, and let him help her to her feet. What she wasn't expecting was when he yanked her towards him and dipped her down at the waist, smothering her sound of surprised as he kissed her a bit more passionately then what might have been necessary. She must have thought so too because when he released her mouth she seemed a bit dazed.

"I don't quite remember that way last time." She said breathlessly. Crowley's ego flared and he smirked at the young woman.

"Well, Love, you didn't bring me any of the 'good stuff' last time." she smiled up at him and a loud cough behind him rudely reminded Crowley that he had an audience. He huffed in annoyance and lifted Ollie back into a standing position. She laughed at his expense before leaning down and grabbing her jacket, swinging it on and rolling her shoulders in adjustment to the weight. She looked between the three men's raised eyebrows and she mirrored them sticking out her hip and placing a hand on it – radiating attitude.

"What?" she demanded. That snapped them out of it and Bobby was the first to respond tapping Dean on the shoulder with his hat before readjusting it.

"Common boys, we've got a hell of a walk on our hands." Dean and Sam looked at each other for a moment then back at Bobby.

"Well Crowley zapped us here he could just- oh." Ollie spun around at Sam's words, realizing that Crowley had indeed zapped somewhere- without them to boot. She laughed and walked over to Dean who still had her bag. Digging into the front pouch she brought out a key ring and shook it teasingly.

"My cars parked down a little ways off road. There's enough room for you three, unless you feel like walking that is." She started walking the way she had come, and Bobby started following but stopped as he realized that Dean and Sam weren't moving. Looking back he followed their gaze to Ollie's ass as it swayed slightly with every step she took. He turned to them, 'I'm gonna kick your ass' written all across his face.

"Boys I'm not telling you again. I don't want to be out here all damn night and I ain't making her wait for you two." That shook them out of their guttered heads and they quickly jogged ahead to walk beside her striking up conversation and making her laugh. Bobby watched them laughing at something she said and shook his head fondly, "Idjits." He stepped up his pace wincing at his joints and soon caught up to them and smacked Dean upside the head when he made a snide remark about his old age.

" **No. Freaking. WAY.** " Ollie turned around from unlocking the door and stared at Dean confused.

"What?" she looked between Dean and her car that he felt the need to drool over apparently. She mistook his amazement and jutted out her hip –a common pose apparently-, "Oh, so I'm a girl who kills for a living but I can't have good taste in cars?" Sam and Bobby rolled their eyes knowingly.

"Dude are you kidding me right now? This is -for real- **your** car?" She smirked amusedly.

"Nope my keys are just irresistible like that. Now if you're done fangirling you mind loading up? I don't know how far away y'all live and I want to find a motel preferably before dawn." With that she climbed in and started up the engine. It's healthy purr echoed and Dean nearly fell down at the sound, or he would have if he hadn't been holding onto Sam's jacket the whole time. Bobby rolled his eyes and slid into shotgun while Sam jumped into the back and Dean had to bite his knuckle to keep from squealing at the suspension when it hardly shifted from his brothers' weight. Even the Baby didn't have suspension like that. Ollie rolled her eyes from the front seat and looked over at Bobby, "Should I be worried about parts of my car missing when I come over?" Bobby shook his head, not taking his eyes off of Dean in case he did something stupid.

"No it's nothing like that, the kid just don't meet that many people as enthusiastic about impala's as he is." Ollie pursed her lips and Sam whistled from the back seat as he rummaged through something and Bobby turned around to glare at him, "Boy ain't anyone ever tell you that messing with peoples things can get you shot?" Ollie revved the gas, watching Dean bite down on his hand as he fanboy'd over the engine.

"Don't worry. Nothing back there accept my cassette tapes." She laughed and Bobby shook his head, she was going to fit right in.

"Yeah, we might want to wait until tomorrow to tell Dean about these." Ollie furrowed her brows at that and looked back at him, "Well this is nearly an exact replica of Dean's collection." Bobby and Ollie both looked at each other then back at Dean. Before she let her hand slap against the steering wheel in defeat.

"Well damn, I don't want to break him or anything." She sighed looking between Bobby and Sam as they tried and failed at hiding their smiles, "What the hell am I supposed to listen to. Pop country?" she shivered involuntarily at mentioning it and Sam shook his head and handed the cassettes to Bobby to decide. The old mans eyebrows shot up to his hairline as he flipped through them. Sam was right it was an exact copy of Dean's collection, except more organized. He looked between the young woman beside him to the tapes and back. She watched him with a confused smirk. "I take it you guys have a pretty stereotypic view on what exactly a woman should drive and listen to?" Bobby laughed and shook his head, not having seen anyone like this kid in all his years.

"Sorry Hon, it's just not that often in our line of work we meet someone like you." He handed the tapes to her and motioned towards Dean, "You better hide those under the seat so he doesn't find them. He'll probably start foaming at the mouth if he does." She started to put them away but stopped. Now most people would think that it wouldn't be possible to out smile the Cheshire cat, but if they had seen Ollie's face right then they would know otherwise. Bobby saw it and nearly shat himself, "Christ girl! You keep leering like that you'll give this old man a heart attack." If anything the smile only widened and she looked between him and Sam, mischief thick in her eyes.

"Whats his favorite song?" Sam took a minute to process what she said but once he did he smiled devilishly, almost matching her own. Bobby saw both of their looks and went from uneasy to horrified in an instant.

"Absolutely not!" he chastised. Turning to Sam he pointed at him warningly, "Samuel Winchester, don't you **dare** tell her!" Sam physically deflated his smile falling as he looked at Ollie in the rearview.

"Sorry no can do, doing something like that would **warrant** me an ass kicking- and what kind of brother would that make me?" Bobby rolled his eyes at Sam's dramatic monotone and Ollie sighed with obviously fake disappointment.

"Well that's too bad… You know, I couldn't help but notice how much he enjoyed that cherry pie earlier." Bobby frowned at her.

"Should I drive, kid? Cause I'm pretty sure that pie was blue-"

"Yeah!" Sam interrupted, "He really loves **pie**." His devilish smile was back and Bobby swore he felt a shiver go down his spine as he watched them in horror. Ollie reached down after a few moments came back up and popped a cassette into the player. Bobby reached over to take it out but she swatted his hand away easily. She turned the car off rolled down the window.

"Lets go man! Moonlights burning away and I ain't wasting my gas sitting here!" Bobby had to cover his mouth with his hand as Dean jogged over taking great care in opening the door and sliding in. He shut the door gently and leaned into the seat, taking in everything like a kid in a candy store; from the vinyl leather seats, the hard wood dashboard and even the studded steering wheel cover. He realized that she was staring at him expectantly. "Well? You want to ogle my car some more or are you gonna put your seatbelt on so we can get the hell out of here?" Dean reached behind him and put his seatbelt on and Ollie nodded in approval making Dean smile back until she said, "Good boy now," she turned and took the car out of park, "Where the hell am I going?" Bobby didn't trust himself to speak so he just pointed left twice and she nodded her head, "Left and onward, alright-y then." She started the car, the engine vibrating as it hummed to life and no sooner had the car started rolling forward then the cassette kicked in with 'Cherry Pie' by Warrant and she gladly sang along

"Dude are you kidding me?" Dean exclaimed as the song ended. She shook her head fervently and he looked like he was on cloud nine, " **You. Are.** _ **Awesome.**_ Who's your favorite singer?" Sam held his breath, praying that she didn't say-

" _Led Zeppelin_ , _Bon Jovi_ , and _Joan and the Blackhearts_." She stated obviously, "I know the last one isn't technically a singer but-"

" **OH MY FUCKING GOD!"** Suddenly a strong pair of arms wrapped around her shoulder and neck making her glide (because she was a professional and professionals don't swerve) into the adjoining lane. Sam tried pulling his brother back but Dean didn't relinquish his hold until bobby slapped him over the head yelling at all of them for being 'complete idjits' and that he would not die with them in a damn car. Ollie and Sam were to busy laughing to hear everything he said and Dean was too stunned to care. Bobby finished his tirade and glared out the window, trying to get his blood pressure under control. Once he was sure he could breath he focused back in on their conversation.

"-you two are seriously evil, I'd be royally pissed if I wasn't so happy. How the hell are you still single?" Ollie laughed and lowered the volume a bit so that they weren't yelling over it.

"Well for one thing, my line of work doesn't exactly make it easy to find people with the same interests and most guys are pretty put off by the fact that I know how to take care of myself. Not to mention I know how to fix a car better then most." Dean shook his head and leaned back in his seat, glowing like the freaking sun.

"On a scale from one to ten how **not** OK would it be if I asked you to marry me?" Bobby scoffed and Sam visibly bristled at the words

"What?" Ollie gasped playfully looking between the road and the rearview mirror, "without all the awkward dating first? The very thought!" Dean leaned forward all serious and asked drastically.

"I have a few questions and you're not going anywhere until they're answered." She smiled and bobbed her head.

"Didn't realize we were quoting Disney but by all means go ahead." Dean smiled whispering 'awesome' before he began his interrogation.

For the next half hour that's how they spent their time going back to Bobby's and in that time they had found out that Ollie was short for Alliadessa (a-lee-a-des-a) she was an Aries (Dean had leaned over and wiggled his eyebrow at that) she was a huge fan of Chevy and that the car they were in was actually a 96 (something about suspension and trunk room) she loved Bacon and tangerines ('but never try them together!') and she preferred knives and daggers over guns and rifles any day of the week. She loved working on any thing with a motor and hunting was a favorite. Sam had decided to tune them out a little while after Dean had started answering her own questions but Bobby's voice pulled him back in.

"So what exactly did you sell your soul for?" there was a moment of silence and Dean spoke up.

"Come on Bobby that doesn't really matter we can talk about it-"

"No he's right." They all stared at Ollie who had her eyes glued to the road, a wistful smile on her face, "I'm actually surprised we went this long without one of you bringing it up… I suppose the only way to understand it is if I tell you everything, but it's a long story full of clichés and sick humor." No one said anything so she nodded her head and sighed.

"My Dad was a contract killer, which is how I got into the business. Mom was supposed to be a job since she was the daughter of a Mafia big shot over in Italy. They did a little bit of Romeo and Juliet action for a while before my dad went up to my grandpa –mom's dad- and told him everything. He was mad at first but respected Dad for growing a pair big enough to tell him everything. Mom told Grandpa that they were going to be married whether he approved or not so he might as well give them his blessing and he did. They got married at the family chapel and hightailed it to Ireland in a small house on an ocean side cliff. Long story short she had my oldest three brothers there –triplets god help her- and they were trouble all three of them. They had her straight black hair and Dads green eyes, lucky bastards. Mom had me after they moved to Hawaii about eight years later and said Dad cried when he held me though I'm not sure I believe it. Another ten years and we were in Italy visiting grandpa when Mom died giving birth to my little sister- curly black hair and blue eyes. Dad was broken hearted and closed himself off- started working jobs again. He put us with our grandpa and though he was a hell of a man he didn't know how to raise us so he started teaching us things. My older brothers chose to go into the family mafia with him and while he and my brothers were away my Great Uncle Franco-"

"Franco?!" Dean shouted laughing, "You had a Great Uncle named 'Franco'?" Sam smacked him and Dean sobered up muttering a quiet sorry.

"Told you it was cliché man." She smiled back at him before going back into her story, "So yeah I called him GUF because that was easier, but anyway he was a car fanatic so he taught me everything he knew. Well I'm a fast learner and a few weeks later I was working in the family garage using a step stool cause I was too damn short to reach anything –the others thought it was a hoot but it pissed me off. Anyway this guy comes in with a fully loaded automatic aiming it right at me and I don't duck or hide or anything. I froze to the spot scared shitless. I hear GUF yelling at me to get down and next thing I know I'm throwing a screwdriver straight into the guys eye. GUF stood there gawking and I thought I messed up or something but a few days' later grandpa and GUF are teaching me how to use knives and the difference in metal and balance, throwing knives and daggers- the works. Dad comes home –finally- and wouldn't you know it I'm a natural. He teaches me a few things and takes me on a few jobs with him. It stayed like that for-oh… about six years. I was sixteen and we were coming home from a job. We walked in and there was so much blood I thought the boys had died the water tank red and released the pipes again but no. They were the first ones we found. The only two alive were GUF and My little sister, and GUF was just barely there. He told us the people responsible were an apposing mafia and that was that. Next morning the world woke up to two mafias gone and a man and his two children MIA. Except he didn't go with them. I was stupid and got in the way and Dad paid for it…" she was silent, her face emotionless as she stared at the road, "… we sank him in the river and moved on. I took my little sister to Kansas and that was that until a man came after us, and I killed him easily enough but it got me thinking that she would never be safe. I'd have to move her place-to-place changing our names and doing all this shit that no kid should have to. Our mom wanted us to be happy, grandpa and GUF too. They used to asked us non-stop if this was the life we wanted and told us they could get us out anytime if we only said so. Well I didn't have grandpa to count on anymore and going to the police?" she scoffed, "So yeah I heard about demon deals from a man –great painter but wasn't known to anyone but god and the demon he sold himself to- and I sold my soul for her to have a life of peace and contentment. I told Crowley I'd give him my soul for her to live a long life of contentment and happiness. He agreed, we kissed, and he zapped her away- erasing her name from the mind of everything and everyone… including myself…" she paused and felt herself continuing before she could stop it, "I remember who she looked like, I remember the sound of her laugh, and how much I love her. I remember loving her like nothing else in this world could ever come close but memories of her are foggy at best- I can't remember anything specific about her, or even where she might be… but demon deals are law and I've got to trust that she's happy wherever she is." the car was eerily silent for quite some time after she had finished and she seemed caught up in her own thoughts until she noticed the three boys staring at her, understanding the loss she went through. Seeing that was almost too much for her.

"… So here I am ten years later getting my soul back with a bunch of redneck supernatural hunters… you still thinking about that proposal **babe**?" she looked at Dean, who was quick to understand and scoffed, leaning back into the seat.

"Yeah well bite me princess." Was his lame counter. She pouted and looked back at him, and had he not known better he would have thought the gleam in her eyes was sadness, not playfulness.

"Aww, sorry Hon. I don't like used meat." Bobby and Sam cackled at Dean's expense as he grit his teeth and tried to get the blush on his cheeks to go away. She laughed and turned up the radio as her favorite song came on and to her pleasant surprise Dean and Sam decided to sing along while Bobby just sat there chuckling.

 _When the clouds they rain down on your parade,_  
 _and wash your float out to the sea,_  
 _You_ _'_ _ve reached your bitter end, but brother you_ _'_ _ve got friends,_  
 _At the drunkard_ _'_ _s damnation jamboree._

 _You can find us there drinking the dog_ _'_ _s hair,_  
 _Hair of that hound that bit you and me,_  
 _Rope and tyin_ _'_ _em on them doggies gettin_ _'_ _gone,_  
 _at the drunkard_ _'_ _s damnation jamboree._

 _We_ _'_ _re getting high, high, high, high,_  
 _Pickin_ _'_ _, drinkin_ _'_ _and singin_ _'_ _songs,_  
 _We_ _'_ _re getting bombed, bombed, bombed bombed,_  
 _Glad you joined us, the night is long._

 _Let_ _'_ _s have another round and spread that joyful sound,_  
 _We may be dead but you must agree,_  
 _Heaven_ _'_ _s not for us, we_ _'_ _re too boisterous,_  
 _At the drunkard_ _'_ _s damnation jamboree._

 _So don_ _'_ _t shed a tear_ _'_ _cause I wound up here,_  
 _Hell ain_ _'_ _t all it_ _'_ _s cracked up to be,_  
 _In fact it_ _'_ _s so much more, they got a music store,_  
 _At the drunkard_ _'_ _s damnation jamboree._

 _We_ _'_ _re getting smashed, smashed, smashed, smashed,_  
 _Cigars and fruit jars of sour mash,_  
 _We_ _'_ _re singin_ _'_ _songs, songs, songs, songs,_  
 _Pour a whisky and sing along._

 _We_ _'_ _re getting high, high, high, high,_  
 _Pickin_ _'_ _, drinkin_ _'_ _and singin_ _'_ _songs,_  
 _We_ _'_ _re getting bombed, bombed, bombed bombed,_  
 _Glad you joined us, the night is long._

 _So when the clouds they rain down on your parade,_  
 _And wash your float out to the sea,_  
 _You_ _'_ _ve reached your bitter end, but brother you_ _'_ _ve got friends,_  
 _At the drunkard_ _'_ _s damnation jamboree_ _…_  
 _At the drunkard_ _'_ _s damnation jamboree_ _…_  
 _At the drunkard_ _'_ _s damnation jamboree_ _…_

 *****Hey! So here's the deal, this was originally meant as a one shot with no real plot or focus but if y'all think it's worth continuing then I'll get a plot and story line started. Just don't hate me if it makes you cry, because I love stories with realist views, not happy endings. So I'm officially opening up a poll for those who do or do not want a continuation. All those in favor please comment as 'Destiel' all those opposed please comment as 'Sabriel'*****

 ******This has nothing to do with my shipping or beliefs in the ship I just assumed it would be funnier because it is and anyone offended please don't be I didn't mean it like that******

 ********P.S I'd like everyone to know that yes _'Drunkard Damnation Jamboree'_ by _Swank_ at the end of the Season Six Supernatural Gag reel montage but I knew this song BEFORE I heard it on there!**

Thanks and I hope you enjoyed!


	2. Update

I know, I know I've been gone so long why bother right? Well recently a friend of mine decide to re-inspire me into my old writing habits and, I gotta say, I retread?

I died inside.

I cringed SO bad guys it ain't even funny. I got a couple people giving a lot of support so in honor of them, I am editing and finishing 'Buisness Transactions and Contracts'.

It's gonna take some time so be patient because I'm in college and I have summer classes so go easy on me and hope you like the edit! I'm gonna keep all the information but release it more slowly so don't worry about it not being the same shitty story.

It will.

Until then!


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